Jrue Holiday is a two-time NBA champion and has designs on competing for a third with the Portland Trail Blazers, which is good news for the Chicago Bulls. If Holiday does indeed help lead Rip City to the playoffs, Chicago would add a valuable first-round pick to its stash in the 2026 NBA Draft.
Then-Blazers president of basketball operations Neil Olshey (who could've given current Bulls executive Arturas Karnisovas a run for his money as far as unpopular front office leaders go) jumped into the trade that sent Lauri Markkanen to the Cleveland Cavaliers in 2021.